34972-56-0Relevant academic research and scientific papers
Novel and facile synthesis of furanodictines A and B based on transformation of 2-acetamido-2-deoxy-d-glucose into 3,6-anhydro hexofuranoses
Ogata, Makoto,Hattori, Takeshi,Takeuchi, Ryota,Usui, Taichi
, p. 230 - 234 (2010)
A novel synthesis of furanodictines A [2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-d-glucofuranose (1)] and B [2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-d-mannofuranose (2)] is described starting from 2-acetamido-2-deoxy-d-glucose (GlcNAc). The synthetic protocol is based on deriving the epimeric bicyclic 3,6-anhydro sugars [2-acetamido-3,6-anhydro-2-deoxy-d-glucofuranose (4) and 2-acetamido-3,6-anhydro-2-deoxy-d-mannofuranose (5)] from GlcNAc. Reaction with borate upon heating led to a facile transformation of GlcNAc into the desired epimeric 3,6-anhydro sugars. The C5 hydroxyl group of the 3,6-anhydro compounds 4 and 5 was regioselectively esterified with the isovaleryl chloride to complete the synthesis of furanodictines A and B, respectively. The targets 1 and 2 were synthesized in only two steps requiring no protection/deprotection.
Thermal decomposition of β-d-galactopyranosyl-(1→3)-2-acetamido- 2-deoxy-d-hexopyranoses under neutral conditions
Chiku, Kazuhiro,Nishimoto, Mamoru,Kitaoka, Motomitsu
experimental part, p. 1901 - 1908 (2010/10/18)
β-d-Galactopyranosyl-(1→3)-2-acetamido-2-deoxy-d-glucose (LNB) and β-d-galactopyranosyl-(1→3)-2-acetamido-2-deoxy-d-galactose (GNB) decompose rapidly upon heating into d-galactose and mono-dehydrated derivatives of the corresponding 2-acetamido-2-deoxy-d-
